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In my experience, rainy days are unpleasant to most. Although there are those who greatly enjoy everything about rainy days – the smell, the feel, the reason – rainy days in the colder months are all around dreary. I’ve also noticed that a great number of men do not carry umbrellas, and neither does our featured Fashionisto.

This week’s Fashionisto keeps it simple with solid colors and matching accent accessories. The first thing I noticed about him was the play on words on his “E.N.E.M.I.E.S.” snapback. If you’ve ever watched the ’90s hit sitcom Friends, then the font and style should look familiar. He layers a plain black crew neck T-shirt with a medium gray zip-up hoodie and a royal blue Diadora windbreaker with black accent colors. He keeps the bottom half of his outfit relatively simple with classic khakis. I say relatively because he is wearing sneakers that are rarely released and highly coveted – Jordan 8 “Playoffs.” If you’re not a “sneakerhead” and you don’t know, “Jordans” are sneakers designed by the Michael Jordan brand and are released with a small supply. The availability heightens the prestige. All in all, this is a quality rainy day outfit — not too much, just enough.

I did some research on the trend of trekking in the rain sans umbrella for men, and I found two examples: American heartthrob and actor, James Dean and the U.S. Army. In an iconic photograph of James Dean, he is walking though the rain with a trench coat, but no umbrella. Many bloggers use this image as evidence to support their claims that men shouldn’t carry umbrellas because it isn’t “cool” — as James Dean is supposedly the epitome of “cool.” In the case of the U.S. Army, the military ruled that military officials on bases or around the Pentagon — not soldiers in trenches — were not allowed to carry umbrellas on the basis that it is “unmanly.” Personally, I think choosing to get wet in the rain is a recipe for catching a cold, but many men continue not to use umbrellas.

If you’re dressed in business or professional attire, carry an umbrella. Showing up to an important meeting or event while soaking wet looks bad. If you care enough to dress nicely, care enough to protect your threads; but if it’s an ordinary casual day, do what you please.

Hint: Depending on the fabric, khakis have the ability to dry quickly after you’ve found cover from the rain. They could be the perfect go-to pants for rainy days. Try not to get too wet, though — some khakis leave water stains.